Assistant Head of Upper School/Dean of Students

Assistant Head of Upper School/Dean of Students

North Shore Country Day

Winnetka, IL

North Shore Country Day School, a JK-12 independent school near Chicago, seeks a dynamic, full-time Assistant Head of Upper School/Dean of Students starting with the 2025-26 Academic Year. While a bachelor’s degree is required, a master’s degree is preferred. North Shore is eager to consider applications from groups traditionally underrepresented in independent school communities. 

Position Description  

The Assistant Head of Upper School/Dean of Students plays a key role in cultivating a positive, inclusive, and accountable student culture while ensuring a dynamic and supportive learning environment. The Assistant Head of Upper School/Dean of Students will collaborate closely with school leadership, faculty, staff, students, and families to build a vibrant student life program and an advisory system that fosters the development of resilient, resourceful, and ethical student leaders. The Assistant Head of Upper School/Dean of Students will report directly to the Head of the Upper School and will serve on the school leadership team.  

A central responsibility of the Assistant Head of Upper School/Dean of Students is to serve as a primary point of contact for both students and families. This includes overseeing the division’s expectations for student behavior and managing the disciplinary process with care and consistency. In addition, the Assistant Head of Upper School/Dean of Students will work alongside the division head to support and enhance the school’s academic mission, ensuring that student well-being is seamlessly integrated with the academic experience.

Essential Position Duties

-Partner with and support the Head of Upper School in maintaining the overall excellence of the Upper School and assume leadership responsibilities in the Head’s absence.

-Establish strong relationships with all members of the Upper School community and serve as a primary point person for addressing student and parent concerns.

-Work closely with students, advisors, and parents to address emotional and situational challenges related to attendance, conduct, and behavioral expectations, prioritizing the use of disciplinary actions as opportunities for reflection, learning, and personal growth.

-Supervise and collaborate with various faculty members to enhance teaching and learning beyond the classroom, focusing on interim week, experiential education days (x-days), and community gatherings

-Participate in the enrollment process as a member of the enrollment committee, working closely with the admissions office to support strategic initiatives and programming for both new and returning students.

-Collaborate with the administrative team and Director of Enrollment in planning, executing, and communicating events and activities related to retention and divisional transition. 

-Lead weekly meetings with Upper School faculty members to discuss students of concern and opportunities for providing proactive support 

-Coordinate support for students in need with counselors, learning specialists, advisors, teachers, etc.

-Collaborate with the Head of Upper School to review the quarterly reporting of grades and progress to students and families.

-Oversee and coordinate the Upper School calendar

-Lead and oversee the strategic vision and annual curriculum for the 9-12 Advisory program. Develop and implement initiatives that foster personal and community relationships, promote a comprehensive student life curriculum, provide academic and emotional support, and guide students through the natural transitions that occur throughout high school.   

-Co-lead the 9th-grade team, designing and facilitating "Introduction to Upper School" sessions that integrate students into the school community while addressing key topics for success in high school and beyond.  

-Play an active role in supporting and mentoring the Upper School Student Council and Upper School Advisory Mentors.

-Design and implement robust programming to support new students' transition into the division, including orientations

Teaching, Coaching & Leadership Outside the Community

-Teach at least one course annually, with assignments determined in collaboration with Administration and Department Heads.  

-Possibly coach one athletic season per year.  

-Serve as an advisor to 7-10 students  

-Actively contribute to fostering a positive school culture by attending and supervising extracurricular and athletic events

Salary Range: $80,000-$100,000

This salary range represents the expected annual salary range for this position. Ultimately, in determining your pay, we'll consider your education level, experience, and other job-related factors.

Candidates are asked to submit a cover letter specific to the role at North Shore Country Day School, a resume, a written statement detailing their philosophy/approach to their work, and a listing of professional references. 

Applications should be submitted electronically at www.nscds.org/about/employment. 

North Shore provides an excellent employee benefits program, including health and retirement benefits, tuition support for children’s attendance at North Shore, and professional development funding to support summer study, attendance at conferences/workshops, travel, and advanced degree work.

We are fully committed to a culturally diverse administration, faculty and student body. North Shore Country Day School is an equal opportunity employer. Employment decisions are based on qualifications, and abilities. North Shore does not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability or any other characteristic protected by law.